1-aminopiperidin-4-ol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 5 mL round-bottomed flask, the above prepared 5-(4-cyano-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid (0.050 g, 155 μmol, Eq: 1.00) was combined with THF (1 mL) and DMF (1 mL) to give a colorless solution. TBTU (74.7 mg, 233 μmol, Eq: 1.5) and N,N-diisopropyl-ethylamine (100 mg, 135 μL, 776 μmol, Eq: 5) were added. The reaction mixture was stirred for 10 min at RT, then 1-aminopiperidin-4-ol (21.6 mg, 186 μmol, Eq: 1.2, CAN 79414-82-7) was added and the reaction mixture kept at RT overnight. Pouring into 25 mL 1 M HCl, extraction with EtOAc (2×50 mL), washing with 1 M NaOH, drying over Na2SO4 and evaporation of all solvents in vacuo, followed by stirring for 15 min with 3 mL of heptane containing 3 drops of EtOAc, generated 51 mg of the title compound as white solid; MS (EI) 421.1 (M+H)+. to give a colorless solution the reaction mixture kept at RT overnight washing with 1 M NaOH drying over Na2SO4 and evaporation of all solvents in vacuo by stirring for 15 min with 3 mL of heptane containing 3 drops of EtOAc

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 5 mL round-bottomed flask, the above prepared 5-(4-cyano-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid (0.050 g, 155 μmol, Eq: 1.00) was combined with THF (1 mL) and DMF (1 mL) to give a colorless solution. TBTU (74.7 mg, 233 μmol, Eq: 1.5) and N,N-diisopropyl-ethylamine (100 mg, 135 μL, 776 μmol, Eq: 5) were added. The reaction mixture was stirred for 10 min at RT, then 1-aminopiperidin-4-ol (21.6 mg, 186 μmol, Eq: 1.2, CAN 79414-82-7) was added and the reaction mixture kept at RT overnight. Pouring into 25 mL 1 M HCl, extraction with EtOAc (2×50 mL), washing with 1 M NaOH, drying over Na2SO4 and evaporation of all solvents in vacuo, followed by stirring for 15 min with 3 mL of heptane containing 3 drops of EtOAc, generated 51 mg of the title compound as white solid; MS (EI) 421.1 (M+H)+. to give a colorless solution the reaction mixture kept at RT overnight washing with 1 M NaOH drying over Na2SO4 and evaporation of all solvents in vacuo by stirring for 15 min with 3 mL of heptane containing 3 drops of EtOAc

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesized in analogy to Example 1 using 5-cyclohexyl-6-(2,2,2-trifluoro-ethoxy)-3-pyridinecarboxylic acid and 1-amino-4-piperidinol (CAN 79414-82-7) as starting materials; LC-MS (UV peak area/ESI) 96.4%, 402.1991 (M+H)+.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesized in analogy to Example 1 using 5-cyclohexyl-6-(2,2,2-trifluoro-ethoxy)-3-pyridinecarboxylic acid and 1-amino-4-piperidinol (CAN 79414-82-7) as starting materials; LC-MS (UV peak area/ESI) 96.4%, 402.1991 (M+H)+.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesized in analogy to Example 1 using 5-(4-chlorophenyl)-6-(cyclobutoxy)-3-pyridinecarboxylic acid and 1-amino-4-piperidinol (CAN 79414-82-7) as starting materials; MS (EI) 402.4 (M+H)+.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesized in analogy to Example 1 using 5-(4-chlorophenyl)-6-(cyclobutoxy)-3-pyridinecarboxylic acid and 1-amino-4-piperidinol (CAN 79414-82-7) as starting materials; MS (EI) 402.4 (M+H)+.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesized in analogy to Example 1 using 5-(4-chlorophenyl)-6-(cyclopropylmethoxy)-3-pyridinecarboxylic acid (CAN 1018782-76-7) and 1-amino-4-piperidinol (CAN 79414-82-7) as starting materials; MS (EI) 402.4 (M+H)+.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesized in analogy to Example 1 using 5-(4-chlorophenyl)-6-(cyclopropylmethoxy)-3-pyridinecarboxylic acid (CAN 1018782-76-7) and 1-amino-4-piperidinol (CAN 79414-82-7) as starting materials; MS (EI) 402.4 (M+H)+.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesized in analogy to Example 1 using 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid (CAN 1018782-82-5) and 1-amino-4-piperidinol (CAN 79414-82-7) as starting materials; LC-MS (UV peak area/ESI) 97.7%, 430.1150 (M+H)+.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesized in analogy to Example 1 using 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid (CAN 1018782-82-5) and 1-amino-4-piperidinol (CAN 79414-82-7) as starting materials; LC-MS (UV peak area/ESI) 97.7%, 430.1150 (M+H)+.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 5 mL round-bottomed flask, the above prepared 5-(4-cyano-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid (0.050 g, 155 μmol, Eq: 1.00) was combined with THF (1 mL) and DMF (1 mL) to give a colorless solution. TBTU (74.7 mg, 233 μmol, Eq: 1.5) and N,N-diisopropyl-ethylamine (100 mg, 135 μL, 776 μmol, Eq: 5) were added. The reaction mixture was stirred for 10 min at RT, then 1-aminopiperidin-4-ol (21.6 mg, 186 μmol, Eq: 1.2, CAN 79414-82-7) was added and the reaction mixture kept at RT overnight. Pouring into 25 mL 1 M HCl, extraction with EtOAc (2×50 mL), washing with 1 M NaOH, drying over Na2SO4 and evaporation of all solvents in vacuo, followed by stirring for 15 min with 3 mL of heptane containing 3 drops of EtOAc, generated 51 mg of the title compound as white solid; MS (EI) 421.1 (M+H)+. to give a colorless solution the reaction mixture kept at RT overnight washing with 1 M NaOH drying over Na2SO4 and evaporation of all solvents in vacuo by stirring for 15 min with 3 mL of heptane containing 3 drops of EtOAc

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesized in analogy to Example 1 using 5-cyclohexyl-6-(2,2,2-trifluoro-ethoxy)-3-pyridinecarboxylic acid and 1-amino-4-piperidinol (CAN 79414-82-7) as starting materials; LC-MS (UV peak area/ESI) 96.4%, 402.1991 (M+H)+.